diff --git a/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/KiloToolWindowFactory.kt b/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/KiloToolWindowFactory.kt
index 93c90aef76f..2356d2a41f0 100644
--- a/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/KiloToolWindowFactory.kt
+++ b/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/KiloToolWindowFactory.kt
@@ -13,9 +13,9 @@ import ai.kilocode.client.agentManager.worktree.WorktreeController
 import ai.kilocode.client.agentManager.AgentManagerPanel
 import ai.kilocode.client.plugin.KiloBundle
 import ai.kilocode.log.KiloLog
+import com.intellij.openapi.actionSystem.ActionGroup
 import com.intellij.openapi.actionSystem.ActionManager
 import com.intellij.openapi.actionSystem.DataProvider
-import com.intellij.openapi.actionSystem.Separator
 import com.intellij.openapi.components.Service
 import com.intellij.openapi.components.service
 import com.intellij.openapi.project.DumbAware
@@ -108,6 +108,8 @@ internal class KiloToolWindowSetupService(
             chat.add(manager.component, BorderLayout.CENTER)
             val agent = object : JPanel(BorderLayout()), DataProvider {
                 override fun getData(dataId: String): Any? {
+                    // Expose the shared manager here too so History works from the Agent Manager tab.
+                    if (SessionManager.KEY.`is`(dataId)) return manager
                     if (SessionManager.WORKSPACE_KEY.`is`(dataId)) return workspace
                     if (SidePanelKeys.MODE.`is`(dataId)) return SidePanelMode.AGENT_MANAGER
                     if (SidePanelKeys.WORKTREE_PANEL.`is`(dataId)) return agentManagerPanel
@@ -143,10 +145,13 @@ internal class KiloToolWindowSetupService(
                 ActionManager.getInstance().getAction("Kilo.NewSession"),
                 ActionManager.getInstance().getAction("Kilo.NewWorktree"),
                 ActionManager.getInstance().getAction("Kilo.History"),
-                Separator.getInstance(),
-                ActionManager.getInstance().getAction("Kilo.Settings"),
             )
             toolWindow.setTitleActions(actions)
+            // Settings moves off the toolbar into the header gear (options) menu: Open Settings…,
+            // Config Files, and Core, inlined from the declarative Kilo.SettingsGroup.
+            (ActionManager.getInstance().getAction("Kilo.SettingsGroup") as? ActionGroup)?.let {
+                toolWindow.setAdditionalGearActions(it)
+            }
         } catch (e: Exception) {
             Telemetry.send("Tool Window Setup Failed", mapOf("stage" to "setup", "errorClass" to e::class.java.name))
             LOG.error("Failed to set up Kilo tool window content", e)
diff --git a/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/actions/HistoryAction.kt b/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/actions/HistoryAction.kt
index f4490febd99..04fb75046a4 100644
--- a/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/actions/HistoryAction.kt
+++ b/packages/kilo-jetbrains/frontend/src/main/kotlin/ai/kilocode/client/actions/HistoryAction.kt
@@ -8,6 +8,8 @@ import ai.kilocode.client.agentManager.SidePanelMode
 import com.intellij.icons.AllIcons
 import com.intellij.openapi.actionSystem.AnAction
 import com.intellij.openapi.actionSystem.AnActionEvent
+import com.intellij.openapi.actionSystem.DataProvider
+import com.intellij.openapi.actionSystem.PlatformDataKeys
 import com.intellij.openapi.project.DumbAware
 
 class HistoryAction : AnAction(
@@ -16,12 +18,23 @@ class HistoryAction : AnAction(
     AllIcons.Vcs.History,
 ), DumbAware {
     override fun actionPerformed(e: AnActionEvent) {
+        val manager = e.getData(SessionManager.KEY) ?: return
         Telemetry.send("History Opened", mapOf("surface" to "tool_window"))
-        e.getData(SessionManager.KEY)?.showHistory()
+        // History renders inside the chat content, which only lives on the AI Chat tab, so bring
+        // that tab forward first when invoked from the Agent Manager tab.
+        if (e.getData(SidePanelKeys.MODE) == SidePanelMode.AGENT_MANAGER) selectChat(e)
+        manager.showHistory()
     }
 
     override fun update(e: AnActionEvent) {
-        e.presentation.isVisible = e.getData(SidePanelKeys.MODE) != SidePanelMode.AGENT_MANAGER
         e.presentation.isEnabled = e.getData(SessionManager.KEY) != null
     }
+
+    private fun selectChat(e: AnActionEvent) {
+        val manager = e.getData(PlatformDataKeys.TOOL_WINDOW)?.contentManager ?: return
+        val chat = manager.contents.firstOrNull {
+            (it.component as? DataProvider)?.getData(SidePanelKeys.MODE.name) == SidePanelMode.CHAT
+        } ?: return
+        manager.setSelectedContent(chat, true)
+    }
 }
diff --git a/packages/kilo-jetbrains/frontend/src/main/resources/kilo.jetbrains.frontend.xml b/packages/kilo-jetbrains/frontend/src/main/resources/kilo.jetbrains.frontend.xml
index 414ab991e0e..209d9d8aff1 100644
--- a/packages/kilo-jetbrains/frontend/src/main/resources/kilo.jetbrains.frontend.xml
+++ b/packages/kilo-jetbrains/frontend/src/main/resources/kilo.jetbrains.frontend.xml
@@ -147,7 +147,8 @@
                 class="ai.kilocode.client.actions.CoreInfoAction"/>
 
         <action id="Kilo.OpenSettings"
-                class="ai.kilocode.client.actions.OpenSettingsAction"/>
+                class="ai.kilocode.client.actions.OpenSettingsAction"
+                icon="AllIcons.General.GearPlain"/>
 
         <action id="Kilo.OpenLocalConfig"
                 class="ai.kilocode.client.actions.OpenLocalConfigAction"/>